With roughly a century of performing under their belts, two songwriting legends graced different Toronto stages Wednesday night. And it wasn't lost on the iconic Gordon Lightfoot.

About a third of the way into his two-hour set before an attentive crowd at an under-capacity Massey Hall, Lightfoot acknowledged “an old friend of ours” in Bob Dylan was playing Air Canada Centre. Then the singer launched into a cover of Dylan's Ring Them Bells which went far better than anticipated.

Thankfully, Lightfoot – who'll be playing at this year's Grey Cup alongside Justin Bieber (yes, you read correctly) -- relied on his own ridiculously rich repertoire to entertain the generations of fans celebrating another string of dates with him at the hallowed venue. In fact, the last of this current four-night run coincides with his 74th birthday.

Despite the fact his pipes aren't quite what they use to be, the singer and his four-piece band churned out plenty of favourites including The Watchman's Gone and All The Lovely Ladies early on. That was of course after the initial standing ovation many gave him before even playing a note.

“Well alright, it's nice to be back,” Lightfoot – wearing a wine coloured jacket -- said to the crowd which included David Suzuki and Don Cherry.

It also appeared that with each passing song Lightfoot's voice improved, particularly on the sweet and folksy Wild Strawberries and Rainy Day People, the latter of which received a warm reception. But it was a string of songs before the intermission which revved things up somewhat beginning with Carefree Highway and continuing with the toe-tapping Cotton Jenny which had some clapping along.

He also let one fan wrap up Ribbon Of Darkness, giving the man a thumbs up and saying “very good.” Yet Lightfoot was in control from start to finish, telling fans asking for If You Could Read My Mind that it was on the horizon, just not yet. When it was performed, it received a well-deserved standing ovation.

The second half was a bit shorter but nonetheless still eventful as the lengthy number The Wreck Of The Edmund Fitzgerald began. Meanwhile the pensive A Painter Passing Through was solid as was the looser, jazzier Baby Step Back. Here Lightfoot nearly cracked up as a lone feather or piece of paper descended from the rafter directly in front of him which he caught sight of.

With one short and sweet singer-songwriting nugget after another given its due, Lightfoot began rounding things off with Early Morning Rain, a tune he described as “not too bad a tune.” Many expected a slightly longer encore but Lightfoot returned for the closing Cold On The Shoulder, taking more bows and shaking hands.

After over 150 shows, it seems neither the artist nor the venue is giving the other the cold shoulder.